Artículo
In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration
Fecha de publicación:
09/2020
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The structural revision of natural (+)-diplopyrone (ND) was achieved by quantum NMR calculations. A DP4/J-DP4/DP4+ tandem suggested 3 as the most likely structure, but ECD calculations did not match the experimental values. The second more probable structure (6epi-1) showed the right ECD spectrum and high DP4/DP4+ probabilities obtained after fitting. However, further analysis of the MTPA-ND derivatives by DP4+/DIP calculations demonstrated that the absolute configuration at C-9 had been incorrectly assigned. Then, the structure of ND was proposed as ent-3.
Palabras clave:
DIPLOPYRONE
,
RELATIVE CONFIGURATION
,
ABSOLUTE CONFIGURATION
,
DP4+
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Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos de INST.DE QUIMICA ROSARIO
Citación
Sarotti, Ariel Marcelo; In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration; American Chemical Society; Journal of Organic Chemistry; 85; 17; 9-2020; 11566-11570
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